889361-56-2Relevant academic research and scientific papers
Efficient access to materials-oriented aromatic alkynes: Via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems
Feng, Chi,Gao, Yunpeng,Ito, Hajime,Kubota, Koji,Seo, Tamae
, p. 430 - 438 (2022/01/22)
Sonogashira coupling represents an indispensable tool for the preparation of organic materials that contain C(sp)-C(sp2) bonds. Improving the efficiency and generality of this methodology has long been an important research subject in materials science. Here, we show that a high-temperature ball-milling technique enables the highly efficient palladium-catalyzed Sonogashira coupling of solid aryl halides that bear large polyaromatic structures including sparingly soluble substrates and unactivated aryl chlorides. In fact, this new protocol provides various materials-oriented polyaromatic alkynes in excellent yield within short reaction times in the absence of bulk reaction solvents. Notably, we synthesized a new luminescent material via the mechanochemical Sonogashira coupling of poorly soluble Vat Red 1 in a much higher yield compared to those obtained using solution-based conditions. The utility of this method was further demonstrated by the rapid synthesis of a fluorescent metal-organic framework (MOF) precursor via two sequential mechanochemical Sonogashira cross-coupling reactions. The present study illustrates the great potential of Sonogashira coupling using ball milling for the preparation of materials-oriented alkynes and for the discovery of novel functional materials.
Facile one-pot syntheses of bromoacetylenes from bulky trialkylsilyl acetylenes
Lee, Taeho,Kang, Hee Ryong,Kim, Shinae,Kim, Sanghee
, p. 4081 - 4085 (2007/10/03)
Because haloalkynes are versatile intermediates in synthetic chemistry, the development of new efficient methods for the conversion of 1-trialkylsilylacetylenes to haloacetylenes in situ remains desirable, especially when the corresponding terminal acetyl
